heelma

For me it worked quite well, but what certainly helped was that my wife has always been into "elegant style", dressing up, etc. She wasn't into heels at all when we met though. My strategy was to convince her that wearing heels simply adds a lot of just that to her overall appearance. Also, I didn't ask her immediately to wear 5" stilettos. I started with buying her 3" block heels, and then over time (maybe over 1 1/2 yrs), they slowly changed to pointy-toe, 4" stilettos. Now, 4.5" is no problem, 5" without platform at special occasions, and I also got her multiple platform heels with up to 5.5 - 6" heels (also more for special occasions). Try to find out how she defines "hooker heels" and then either avoid asking her to wear those styles or do baby steps towards them. For example, I know she would never want to wear clear plastic heels/platforms or thigh boots. Of course, she knows that I love it when she wears sexy heels, and I told her that from the beginning on as well.
In conclusion, she may have a desire to dress up and care to look good to begin with, and then you have to convince her that heels strongly add to elegance. So, instead of asking her to wear them because you like them, you'll teach her to like them herself! Plus, go small steps and take your time.
Another aspect: though she doesn't know that I like to wear heels also (though rather occasionally only), I found it very helpful to try certain styles of shoes myself and find out their pros and cons, so that I know which problems can occur that would bother her; and those are the styles that I avoid buying her then. With "styles", I don't mean a specific shoe, but rather to see the difference between chunky heel and stiletto, platform vs. no platform, Mary-Jany vs. pumps, etc.